ISSN:
1434-4475
Keywords:
Pleuromutilin
;
Inversion of configuration
;
1,5-Hydride-shift
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The contact of pleuromutilin derivatives with the protein moiety of cytochrome P-450 as well as its orientation towards the heme iron is mainly dependent on the steric environment of the hydrindanone-part of the tricyclus. The apparent affinity between substrate and enzyme, which is correlated with the rate of metabolism can be reduced by inversion of configuration at carbon 6. This inversion is achieved by equilibrating the diastereomeric ketones12 and13 followed by a selective reduction of the keto group at position 7. The 6-methylgroup of14 was assigned α-configuration on the basis of spectroscopic data in comparison to those of the naturally configurated compound14a.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00799036